4-Methylmorpholine → HCID 67266905, compound

HRID 602801Notes

Reaction equation

HRID 602801 reaction equation
[C:1]1([S:7]([CH2:10][C:11]([NH:13][NH2:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:15]C(C1C=CC=CC=1)C(O)=O.ON1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2N=N1.CN1CC[O:40][CH2:39][CH2:38]1.CCN=C=NCCCN(C)C.[NH4+].[Cl-]>C1COCC1>[I:15][C:30]1[CH:35]=[CH:34][C:33]([CH2:38][C:39]([NH:14][NH:13][C:11](=[O:12])[CH2:10][S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])=[O:9])=[O:40])=[CH:32][CH:31]=1

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 9943159Iodophenylacetic acidHCID 11378890Benzenesulfonyl-acetic acid hydrazide

Product 1

HCID 67266905HCID 67266905, compoundYield 469.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1 g (4.7 mmol) of benzenesulfonyl-acetic acid hydrazide (example 74.1) in 4 mL of THF was treated with 391 mg (4.7 mmol) of iodophenylacetic acid, 126 mg (0.93 mmol) of 1-hydroxybenzotriazole and 2.8 g (28 mmol) of N-methylmorpholine. The mixture was stirred during 15 min at 0° C., treated with 1.25 g (6.5 mmol) of EDCI and stirred during 12 hrs. The crude was treated with diluted aqueous NH4Cl and extracted twice with EtOAc. Drying of the combined organic layers over Na2SO4, filtration and evaporation gave 2 g (93%) of benzenesulfonyl-acetic acid N′-[2-(4-iodo-phenyl)-acetyl]-hydrazide as a brown oil, MS: 266 (MH+)

Workup

  1. stirringstirred during 12 hrs
  2. extractionextracted twice with EtOAc
  3. dry with materialDrying of the combined organic layers over Na2SO4, filtration and evaporation

Sources & evidence

ORD record
ord-184aee9abcfc4afcbfcf236f9652ebda
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

Loading…